Water → 2-Chloro-4-methoxyphenoxy-1,3-thiazole

HRID 404875Notes

Reaction equation

HRID 404875 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[OH:10].Br[C:12]1[S:13][CH:14]=[CH:15][N:16]=1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[O:10][C:12]1[S:13][CH:14]=[CH:15][N:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 764302-BromothiazoleHCID 874592-Chloro-4-methoxyphenol

Product 1

HCID 694346862-Chloro-4-methoxyphenoxy-1,3-thiazoleYield 88%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 2-chloro-4-methoxy-phenol (7.93 g, 0.05 mol), 2-bromothiazole (9.0 g, 0.055 mol) and potassium carbonate (7.6 g, 0.055 mol) in dimethyl sulfoxide was heated at 160° C. under nitrogen for 4 hours. The solution was cooled and treated with water, and the aqueous phase was extracted with dichloromethane. The organic layer was washed with brine, dried and concentrated to give 30 g of the crude material, which was purified on a silica gel (ethyl acetate/hexane 5-35%) to afford 10.62 g of the product as a light yellow oil (88% yield), 1H NMR (300 MHz, CDCl3) δ ppm 3.81 (s, 3H) 6.80 (d, J=4.04 Hz, 1H) 6.85 (dd, J=9.19, 2.94 Hz, 1H) 7.01 (d, J=2.94 Hz, 1H) 7.19 (d, J=3.68 Hz, 1H) 7.27 (d, J=8.82 Hz, 1H). MS (ESI), m/z 241.9 (M+H)+.

Workup

  1. temperatureThe solution was cooled
  2. extractionthe aqueous phase was extracted with dichloromethane
  3. washThe organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customto give 30 g of the crude material, which
  7. customwas purified on a silica gel (ethyl acetate/hexane 5-35%)

Sources & evidence

ORD record
ord-e96536f28e7e44099f3ffc5d2ad60d32
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Reaction notes

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